1-Naphthylamine
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| Template:Longitem | C10H9N |
| Molar mass | 143.19 g/mol |
| Appearance | Colorless crystals (reddish-purple in air)[1] |
| Odor | ammonia-like[1] |
| Density | 1.114 g/cm3 |
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| Vapor pressure | 1 mmHg (104°C)[1] |
| Template:Longitem | Template:Plainlist |
| Template:Longitem | 2-Naphthylamine 1-Naphthol Naphthalene Aniline 1,8-Bis(dimethylamino)naphthalene |
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1-Naphthylamine is an aromatic amine derived from naphthalene. It can cause bladder cancer (transitional cell carcinoma). It crystallizes in colorless needles which melt at 50 °C. It possesses a disagreeable odor, sublimes readily, and turns brown on exposure to air. It is the precursor to a variety of dyes.[2]
Preparation and reactions
It can be prepared by reducing 1-nitronaphthalene with iron and hydrochloric acid followed by steam distillation.[2]
Oxidizing agents, such as ferric chloride, give a blue precipitate with solutions of its salts. Chromic acid converts it into 1,4-naphthoquinone. Sodium in boiling amyl alcohol reduces the unsubstituted ring, giving tetrahydro-1-naphthylamine. This tetrahydro compound yields adipic acid when oxidized by potassium permanganate.
At 200 °C in sulfuric acid, it converts to 1-naphthol.
Use in dyes
The sulfonic acid derivatives of 1-naphthylamine are used for the preparation of azo dye. These compounds possess the important property of dyeing unmordanted cotton.
An important derivative is naphthionic acid (1-aminonaphthalene-4-sulfonic acid), which is produced by heating 1-naphthylamine and sulfuric acid to 170–180 °C in the presence of crystallized oxalic acid. It forms small needles, very sparingly soluble in water. Upon treatment with the bis(diazonium) derivative of benzidine, 1-aminonaphthalene-4-sulfonic acid gives Congo red.
Safety
It is listed as one of the 13 carcinogens covered by the OSHA General Industry Standards.[3]
See also
- Used in preparation of aptiganel.
References
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